Formic Acid → HCID 88420577, compound

HRID 2292581Notes

Reaction equation

HRID 2292581 reaction equation
C1(C([NH:20][C:21]2[S:22][CH:23]=[C:24](/[C:26](=[N:56]/[O:57][CH3:58])/[C:27]([NH:29][CH:30]3[C:37](=[O:38])[N:36]4[CH:31]3[CH2:32][S:33][C:34](/[CH:46]=[CH:47]/[CH2:48][S:49][C:50]3[N:54]([CH3:55])[N:53]=[N:52][N:51]=3)=[C:35]4[C:39]([O:41]C(C)(C)C)=[O:40])=[O:28])[N:25]=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)=O>O>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:56]/[O:57][CH3:58])/[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34](/[CH:46]=[CH:47]/[CH2:48][S:49][C:50]2[N:54]([CH3:55])[N:53]=[N:52][N:51]=2)=[C:35]3[C:39]([OH:41])=[O:40])=[O:28])[N:25]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 88420045HCID 88420045, compound

Product 1

HCID 88420577HCID 88420577, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

329 mg of the compound of Step A and 9.6 ml of a 33% aqueous solution of formic acid were mixed together and heated for 25 minutes at +65° C., then cooled, diluted with water, filtered, and concentrated to dryness by distilling under reduced pressure. The residue was triturated in water and the insoluble matter formed was eliminated by filtering, and after concentrating to dryness, 142 mg of 7-[2-(2-aminothiazol-4-yl)-2(Z)-methoxyimino-acetamido]-3-[3-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)thio-propen-(E)-yl]-8-oxo-4-thia-1-azabicyclo [4,2,0]oct-2-en-2-carboxylic acid with a specific rotation of [α]D20 =-99° (c=0.8% DMSO) were obtained.

Workup

  1. temperatureheated for 25 minutes at +65° C.
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. distillationby distilling under reduced pressure
  6. customThe residue was triturated in water
  7. customthe insoluble matter formed
  8. filtrationby filtering
  9. concentrationafter concentrating to dryness, 142 mg of 7-[2-(2-aminothiazol-4-yl)-2(Z)-methoxyimino-acetamido]-3-[3-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)thio-propen-(E)-yl]-8-oxo-4-thia-1-azabicyclo [4,2,0]oct-2-en-2-carboxylic acid with a specific rotation of [α]D20 =-99° (c=0.8% DMSO)
  10. customwere obtained

Sources & evidence

ORD record
ord-482437607e874584abda82e50e8ef256
Source dataset
uspto-grants-1997_11
Patent number
US05683996

Reaction notes

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